Noel: Tim, there’s a lot to talk about with White Men Can’t Jump—the racial politics, the early-1990s signifiers, the way writer-director Ron Shelton fills the movie with basketball lingo without feeling the need to over-explain any of it—but I want to begin at the beginning, with an opening 10 minutes that could teach a lot of filmmakers how to start a movie.

Shelton gives a taste of Venice Beach via brief, impressionistic flashes of its artists, eccentrics, and street performers, set to a soft a cappella soul song (much gentler than the the uptempo funk that’s going to dominate the soundtrack, and quieter than the movie’s overall tone). Then he introduces Woody Harrelson’s Billy Hoyle, an athlete with a superiority complex. After Billy lies down on the asphalt—directly under a hoop, looking up at the blue skies and basketball gods—Shelton cuts abruptly to the action and patter of a game in progress, focusing primarily on Wesley Snipes’ Sidney Deane, a preening stud with slick moves and a keen shooting eye. And when I say “action and patter,” I mean the latter more than the former. In White Men Can’t Jump, basketball is largely a game of words, pausing regularly for insults, curtain calls, arguments over fouls, negotiations over the actual score, and even brief flashes of “So how have things been going with you?” conversation.

Just when it looks like Billy’s been forgotten, the camera catches him sitting on a bench, watching the game, about to be called in to replace one of Sidney’s opponents. Billy’s “who, me?”/“aw shucks” routine quickly gets under Sidney’s skin—especially when the white boy starts beating him—until he drops the act and shows that he’s a hustler who can match Sidney shot for shot and diss for diss. There’s not a lot of throat-clearing in the early going of White Men Can’t Jump. Shelton knows what the strength of this movie’s going to be—basketball and banter—so he jumps right into it, establishing the milieu and the characters on the fly.

When critics write about Shelton’s best films (which in my opinion are Bull Durham, Tin Cup, and this one), the focus is usually on his snappy dialogue, and his unique conflation of sports, romance, and philosophy. But I’m not sure Shelton gets enough credit for some of his other qualities, like his pacing, his structure, and his sense of when to thrust the viewer into the middle of the action and when to stand back. There’s a scene later in White Men Can’t Jump where Sidney gives Billy three chances to prove he can dunk, and after staying in close on the first two attempts, Shelton shows Billy’s last miss—the one that costs him dearly—in a longer shot, capturing more fully the darkness of the court and the matter-of-factness of the failure.

Before we get into everything that this movie’s trying to say, can we take a moment to tip our brightly colored backwards baseball caps to how well Shelton says it?

Tim: You’re right, Noel: The first 20 minutes of White Men Can’t Jump could almost be a self-contained short. It establishes both of its central characters perfectly—not to mention creates a terrific sense of place—and even has its own dramatic arc with a beginning, middle, and end. Shelton’s storytelling is incredibly economical, letting action define character superbly.

I haven’t watched White Men Can’t Jump since it came out in 1992, but seeing it this time, I thought of two very different movies with equally terrific scene-setting openings—California Split and Whiplash—and realized that Billy and Sidney’s odyssey overlaps with the characters’ in those films. Like California Split’s Bill and Charlie and Whiplash’s Andrew and Fletcher, these basketball hustlers operate in a specific subculture that they’ve turned into an art form—so much so that they can’t function in the conventional real world anymore.

That theme connects most of Shelton’s movies: guys who are great at sports and nothing else. In Bull Durham and Tin Cup, the main characters find a way to grow by falling in love with a good woman, while in the biopic Cobb, Ty Cobb’s inability to transcend his S.O.B.-ness is part of the man’s fatal failing. (Although it’s worth pointing out that a brand-new Cobb biography pushes against that popular perception of the man.) But White Men Can’t Jump occupies an intriguing middle ground between those two extremes: It’s a comedy that’s actually pretty sad.

At the time of the film’s release, critics tended to agree that White Men Can’t Jump’s opening was its strongest section, which might be intentional but is also the movie’s lagging limitation. Billy and Sidney are happiest on those outdoor courts, talking shit and playing like little kids. The outside world intervenes briefly—Sidney’s wife Rhonda (Tyra Ferrell) stops by because her check bounced, a reminder of the family’s meager financial situation—but otherwise, the film’s opening is these men’s version of heaven.

The rest of the movie serves as a reminder that Billy and Sidney can’t escape reality. Sidney has several jobs but doesn’t have enough in the bank to afford a house in a safer section of Los Angeles for his family, and Rhonda is losing patience with his focus on basketball. But he’s a model of maturity in comparison to his partner: Billy owes a lot of money to mobsters, is dating a possible alcoholic (Gloria, played by Rosie Perez) with get-rich-quick schemes, and probably has an undiagnosed gambling addiction.

Shelton treats these plot points as deceptively, sometimes irritatingly zany—Billy and Gloria dash away from the mobsters in madcap fashion, Gloria inexplicably ends up on Jeopardy!—but White Men Can’t Jump’s intermittent success at recapturing the zing of its opening sequence does nothing to diminish the characters’ nagging desperation. As you mentioned, Noel, Shelton shows off his usual gift for dialogue, but it’s in service of men whose verbosity becomes emptier as the film goes along. Early on, Billy criticizes Sidney’s flamboyant style, saying that, like lots of black players he knows, “You’d rather look good and lose than look bad and win.” It’s the key difference between the two men and their dilemmas. For all of Sidney’s bluster, he’s actually a grownup who can’t accept the fact that he’s an adult. But Billy really is an overgrown child, his dopey demeanor not an act but, rather, a state of permanent adolescence. On some level, Sidney can afford to lose at basketball—he has real responsibilities—while Billy’s entire livelihood is based on his ability to win money hustling other players.

Since you mentioned it, Noel, I’m curious about your take on the film’s racial politics and, as you put it, “early-1990s signifiers.” Cards on the table, I found White Men Can’t Jump surprisingly prescient in its depiction of a multicultural big city in which the have-nots have to scrape to get by—and yet shockingly dated in its “white people are like this/black people are like that” simplification of race relations. How did it land for you?

Noel: Oh, I wouldn’t say “shocking,” necessarily. But then I have a soft spot for 1970s sitcoms and game shows, where the racial humor is often more refreshingly confrontational than it is today. Plus, I think there’s a certain amount of posturing on Billy and Sidney’s part when it comes to their personae. They’re staying in their assigned roles so they can turn it to their advantage later if need be. Note that even though Sidney gets in Billy’s head during the dunking contest by saying, “White men can’t jump,” that scene comes just a few minutes after he fed Billy a pass at the “Brotherhood Tournament,” expecting him to jam it.

If anything, I’m surprised Shelton doesn’t do more with the race jokes, given both the film’s title and when it’s set. This is unmistakably an early-1990s movie just going by the outfits, which have that particular mix of crossover hip-hop/pop style and leftover 1980s Day-glo. (And that’s without even getting into the now-quaint-looking “Parental Advisory” T-shirt.) But isn’t it a little odd that Billy and Sidney’s big musical argument is about Jimi Hendrix, and not, say, Public Enemy or Beastie Boys? In an era when white people were appropriating black culture like crazy, surely there was something other than basketball and a 1960s rocker that these two guys could stubbornly claim as their own.

I do agree with you, though, that White Men Can’t Jump is a lot savvier about the meaning of money than I’d recalled from the last time I saw it (which was more recently than you, though still at least five or 10 years ago). In the decades since it came out, I’ve been quoting Rhonda Deane’s line about the Vista View apartments, “There ain’t no vista, there ain’t no view, and there certainly ain’t no vista of no view.” But I’d forgotten about the cruddy motels Billy and Gloria live in, and about Sidney’s three off-the-books non-basketball jobs, and about how much the targets of the hustles have to scramble to acquire the dough they lose.

I also agree with you about the movie’s increasing shagginess, post-opening. It gets awfully plotty down the stretch; and some of Billy and Sidney’s schemes seem awfully far-fetched, given how much they rely on their opponents to commit the same blunders over and over. Plus, the script makes some assumptions about how Jeopardy! works that fans of the show (such as myself) may find distracting (such as I do).

But to be fair, Shelton’s never been overly concerned with plot. He’s more interested in maneuvering people with conflicting worldviews into the same place at the same time, and seeing how they react. And it’s not just Billy and Sidney who are at loggerheads. Billy and Gloria have different takes on sex and gender roles, and Gloria and Rhonda differ on whether getting paid matters more than loyalty. Tim, you compared the romance-driven plots of Shelton’s sports films, but would you agree that what also unifies his best films is how his characters are all idealists of a kind, each convinced that whatever they’ve figured out so far about how to live is all anyone needs to know?

Tim: For me, what’s shocking about White Men Can’t Jump’s depiction of race is that the film came out just a month before the L.A. riots. Shelton couldn’t have known what would later occur while he was making the movie, but I couldn’t help but see unconscious clues into future societal unrest within the movie.

Some are very well done. Shelton has a great throwaway moment when the white organizers of the two-on-two tournament mumble, “Let’s get the hell out of here” after Billy sinks the game-winner—a clear sign that their high-minded talk about the event “promoting brotherhood among us all” is just lip service. (Also funny: When the “brotherhood” line is originally spoken, Shelton cuts to a handful of black men shaking their heads, one of the guys saying, “That’s bullshit…”) But earlier in the movie, Shelton has Marques Johnson’s Raymond, who needs money to match Sidney’s bet, put on a ski mask and pull a gun on a local convenience-store owner he knows. The filmmaker is playing with negative media images of blacks, but the joke lands awkwardly, the laugh getting lodged in the throat.

And I agree with you, Noel, about the odd use of Hendrix as Sidney and Billy’s big musical bone of contention. I suspect that either Shelton wasn’t hip to Public Enemy or wanted to go with a safer choice that a wider, whiter audience would recognize.

As for Shelton’s idealists, I think that’s a great observation. Since we’re both sports guys, I know you’ll get what I mean when I say that Shelton’s characters often seem to have the same tunnel-vision mindset that most professional athletes have. Superstitious by design, creatures of habit, and purveyors of just-one-game-at-a-time platitudes, athletes often operate in the vacuum of their own talent, learning to focus only at the task at hand so as not to be taken down by the ever-present danger of “distractions.” Also, because superstar athletes are treated like gods from childhood, they can’t help but fall victim to their own hype, existing in worlds of privilege in which their natural talent is all they need to negotiate through life.

You described Shelton’s characters as being “convinced that whatever they’ve figured out so far about how to live is all anyone needs to know.” That’s right, and it’s a very sports-centric way of thinking, which is actually a deliberate form of non-thinking. Shelton’s movies often tackle this problem. One of Bull Durham’s main plotlines is Kevin Costner helping Tim Robbins’ oddball pitcher get over his mental hang-ups. In Tin Cup, Costner is a once-great golfer who stubbornly refuses to “lay up” because he feels that’s the coward’s way of golfing.

In sports, there’s a lot of talk about athletes’ biggest obstacle being “between the ears”—meaning, the mental component. It’s the one area where athletes aren’t in complete control of their gifts, and we both could name countless examples of athletes who lost their way after they retired from sports, no longer able to rely simply on talent to coast through life. Shelton’s athletes rarely hit the big time, so they’re stuck in the real world, which is probably why his characters are often struggling. (Even in Cobb, the great slugger’s on-the-field achievements are less important than his personal problems. Actually, Cobb is the great exception in Shelton’s oeuvre: He’s the one staunch anti-idealist.) Shelton’s characters live in their narrow worldviews, but Shelton has the proper perspective to look at their situation with insight, but also compassion. He loves his characters too much to mock them. (This tendency extends even to his “30 For 30” documentary about Michael Jordan’s ill-advised attempt at a baseball career, Jordan Rides The Bus, which is about the biggest sports star in the world getting humbled.)

Even though White Men Can’t Jump is 23 years old, one thing that hasn’t aged a bit about the film is men’s absolute devotion to basketball. The superstars have changed, but the NBA remains (behind the NFL) America’s most popular sport. I was wondering, Noel, if there’s anything about the film’s depiction of sports, fandom, or athletes that hit you differently now as an adult then when you saw it as a kid. Do you envy the idealism of Shelton’s characters? Or does being a father and a husband change your perspective?

Noel: Being a family man may have given me a different slant on Sidney, who is much better than Billy at compartmentalizing his life. Sidney’s not the same man on the court that he is with his wife and kid, or when he’s talking to one of his business clients. Billy, on the other hand, can’t keep any of his promises to Gloria because he rarely thinks too far beyond what he wants to do at any given moment—or what he’s stupidly sure he needs to do. In the post-Jeopardy! scene, after Gloria’s taken Billy back, she wants him to buy some nice clothes for job interviews and he looks dumbfounded, as though he assumed that just not gambling away all their money would be enough to prove that he’d grown up.

I’d like to believe that I’m more a Sidney than a Billy when it comes to looking at the bigger picture, though I’ve sure known a lot of Billys who think they’re standing up for a principle when they’re really sacrificing what they want in order to satisfy their egos. It’s ironic that when Billy rags on Sidney soon after they first meet, he snarls, “How many dinners did this chain set your family back?,” when really Sidney is the fiscally responsible one.

So no, I don’t really envy how committed these guys are to their causes, though I damn sure envy their ability to ball. I’ve never been a talented athlete—I play hard, but have no stamina, no discipline, and no talent—so the most I can really relate to Billy and Sidney is when they’re jawing at each other, throwing around insults, impressive-sounding-but-meaningless jargon, and silent looks of disgust. (Y’know, the way that buddies do.) Shelton has an uncanny ear for that kind of dialogue, whether Billy’s complaining that Sidney isn’t “d’-ing up” or Sidney and his friends are stringing together impromptu nonsense like “ain’t no thing but a chicken wing on a string.”

Again, though, what I love about White Men Can’t Jump is that Shelton lives up to that chatter with the thrilling basketball footage. You ask what strikes me differently now about the movie’s depiction of the game, and I’d have to say that I’m more impressed than ever by the physicality. I’ve watched a lot of basketball movies lately, and lesser directors tend to emphasize “the big shot,” in the same way that poker movies tend to think that being a really good professional gambler involves catching a miracle card whenever you need one. Shelton has shooting, dunking, passing… all the usual hoops stuff. But he spends just as much time away from the ball, where players are grabbing and pushing each other. That’s where the battle’s really fought, between people trying to force some separation.

It’s easy to wax rhapsodic about baseball, as Shelton does in Bull Durham, because that’s a sport with more discrete plays and moments of clearer heroism or failure. But in White Men Can’t Jump Shelton finds the beauty in the the great shoving match that is big-boy basketball. He stands with Gloria when she levels her most devastating criticism of the way that Sidney keeps taking advantage of Billy: “It’s not artistic.” Playing with style and grace matters as much to Shelton as finishing with the higher score.

Tim: Yeah, it’s pretty easy to see White Men Can’t Jump as a metaphor for (and a warning against) following your creative aspirations. In a way, Sidney and Billy are like every adult I know who’s still trying to produce a screenplay or get his band to the next level: Their dreams didn’t exactly work out, but that doesn’t mean they’re going to drop them completely. Basketball is an artistic calling for these men, and for them “growing up” means giving up an essential element of who they are. That understanding makes their shit-talking all the more urgent and poignant: It comes from a place of love.

I wouldn’t want to oversell my athletic abilities, but as a kid I was just good enough (and plenty tall enough) to play basketball consistently through my early 20s. My shot was inconsistent—Billy and Sidney’s best-of-five showdown at the opening always stresses me out because I was terrible at that—but I was tenacious, always getting back on defense and grabbing rebounds. Never being very bulky, I would be eaten alive in the world of White Men Can’t Jump, and the few times I’ve had a chance to watch streetball here in Los Angeles, I’m always impressed with the warrior mentality of the players. That’s a small but crucial element that Shelton gets absolutely right: that combination of swagger and toughness of the guys on the court.

It’s funny, though: White Men Can’t Jump made me want to play basketball for the first time in forever, just because I’d be curious how well I’d hold up. It’s probably best I don’t find out. (And, Noel, I don’t buy for a second your protestations about your mediocre skills. This whole movie is about conning the other player, and I’m not falling for it.)

My final observation about White Men Can’t Jump is that it was impossible to re-watch the movie and not think about what’s become of the two stars since 1992. Back then, Wesley Snipes was a star on the rise, having been great in Jungle Fever and New Jack City the previous year. (For good measure, in ’92 he also did an indie drama, The Waterdance, and an action movie, Passenger 57.) It seemed like he was going to be huge. Well, that didn’t quite work out. As for Woody Harrelson, when White Men Can’t Jump came out, he was showing another side of himself: We all knew him as the sweet, lovable dope Woody from Cheers, not some hustling b-baller. From there, Harrelson would further push against that corn-fed persona in movies like Natural Born Killers and The People Vs. Larry Flynt.

That knowledge adds a note of wistfulness to White Men Can’t Jump, which is partly about the fact that we can’t stay young forever. And it makes me wonder where Sidney and Billy are today. They’re probably as excited as I am for the NBA Finals. And they probably drive the younger guys nuts on the Venice Beach courts, endlessly talking smack about how much better they were back in the day. Some guys never change.

Scott kicked off the White Men Can’t Jump conversation yesterday with his Keynote essay on how the film contemplates the meaning of winning. And come back tomorrow when we run down the scores on basketball movies in our periodic By The Numbers feature.